How AI can streamline peak season post-purchase logistics operations

By Oscar Sanchez Duran, Director Analyst, Gartner Supply Chain

The holidays are upon us, and for retailers, that means a tidal wave of online orders, often arriving in a rush during the final stretch of December. Last year, U.S. holiday e-commerce sales climbed by double digits, and experts expect similar growth this season. With rising order volumes come rising risks: labor shortages, overstretched customer-service teams and, most of all, an avalanche of “Where is my order?” calls and returns that threaten both margins and brand loyalty.

During busy stretches like the holiday season, retailers should prioritize post-purchase AI strategies that can turn last-mile headaches into customer-love opportunities. According to Gartner survey data, improving customer experience through more service choices is now the top priority for logistics leaders over the next five years. By embedding AI and GenAI agents into the post-purchase delivery process, brands can defuse tension, delight shoppers and even drive incremental revenue.

Why post-purchase matters more than ever

During peak shopping seasons, shoppers still expect delivery service times to work as usual, even for next-day or same-day delivery. Anything less feels like a broken promise, one that can cost a retailer repeat business or damage their reputation. A Gartner survey shows that “improving customer experience” outpaced digitalization, automation and resilience as the number one priority in logistics functions.

Cart abandonment studies confirm that when shoppers see unclear delivery options, they often exit before checkout. When they do buy, every missed delivery window or delayed status update can become a reason to switch to a competitor offering greater transparency. To address the challenge, retailers must embrace post-purchase delivery experience solutions (PPDE) to meet surging expectations, minimize customer-service load and protect profit margins.

The AI advantage in reducing WISMO calls

“Where Is My Order?”—or WISMO—has long been the bane of both customers and support agents. During peak season, WISMO calls can spike significantly, clogging phone lines and frustrating shoppers waiting for gifts to arrive.

By integrating the PPDE’s AI agents into the tracking portal or social chat platforms, retailers deflect low-value calls and messages away from live representatives. Those AI agents can tap into real-time carrier data, forecast delivery windows with machine learning accuracy and even suggest alternate pickup points if a first-attempt delivery fails. The result is leaner customer service teams, shorter wait times for genuine escalations and lower operating costs at the holiday’s busiest juncture.

However, logistics leaders should evaluate and plan for certain risks before scaling these solutions. Some customers may resist AI-driven interactions, preferring human support for reassurance during high-stakes periods like holidays. Over-reliance on AI agents without clear fallback options can lead to customer frustration if the system misinterprets queries or fails to resolve issues.

Additionally, using large language models introduces data privacy and compliance considerations, and inaccurate responses can harm brand perception rather than enhance it. A balanced approach, combining automation with accessible human escalation paths, can help mitigate these risks while delivering efficiency gains.

Personalization & engagement that drives repeat purchases

Popular shopping seasons aren’t just about one-and-done sales; it’s a prime opportunity to drive incremental revenue through upsells and cross-sells. PPDE solutions with AI and customer profiling capabilities can insert targeted marketing banners and personalized communications into post-purchase notifications and web portals. A shopper who just bought a child's winter hat, for example, could receive a 15% off offer on matching mittens served via the same AI agent that confirms their delivery status.

This integration of logistics and marketing allows order-status updates to serve as communication points. PPDE solutions can include customer profiling and engagement analytics, enabling brands to experiment with seasonal options such as gift wrap, faster shipping for small items, or extended warranties on electronics, and track responses in real time. These approaches help make transactional messages more personalized and maintain customer engagement within the shopping experience.

Flexible returns: Turning returns into brand-loyalty opportunities

Returns are a challenge anytime, but especially during peaks like the holidays when return volumes can soar. PPDE solutions can provide returns enablement capabilities to streamline the return process and create a more positive experience for customers. Rather than forcing shoppers into a one-size-fits-all process, the technology provides different options for brands to deliver a more personalized return journey. This can include generating customer return labels for mail-back, identifying the nearest in-store or drop-off points, and in some cases, suggesting instant exchanges or complementary items.

By automating and simplifying much of the process, retailers can reduce return friction and salvage sales that would otherwise walk out the door. During the holidays, when customer patience runs thin, an efficient AI-powered process can help resolve issues and strengthen brand loyalty beyond the season.

Transform logistics post-purchase processes with AI

The key to capturing the full upside of PPDE lies in a strategy that seamlessly weaves together tracking, returns and branded customer engagement, with AI capabilities embedded from the start.

To begin, start by auditing carrier coverage and piloting a single use case, such as AI chatbots for WISMO deflection and personalized communication. Throughout a stretch like the holiday season, feed your AI agent holiday-specific scripts with delivery cutoff dates, weather-delay alerts and festive return terms to keep interactions timely and on-brand. Then fine-tune its voice with seasonal greetings, gift-wrap tips and upbeat phrasing that mirror your marketing campaigns.

By taking steps now, organizations will be poised to scale customer experience during the delivery process with AI-driven personalized notifications and options, ensuring logistics operations are future-proofed for peak demand.

About the author

Oscar Sanchez Duran is a director analyst in Gartner’s Supply Chain Practice. He conducts research in the supply chain area focused on transportation within logistics with specific focus on transportation technology and international shipping compliance.

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